(2-Methyl-pyrrolidin-2-yl)-phosphonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester ethyl ester | 872605-87-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (2-Methyl-pyrrolidin-2-yl)-phosphonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester ethyl ester
• 英文别名: 2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-ethoxy-oxidophosphaniumyl]-2-methylpyrrolidine
• CAS: 872605-87-3
• 化学式: C₃₄H₆₀NO₃P
• 分子量: 561.829
• InChiKey: LZJGXEQKPLRRSI-XTBUJPMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  53.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-Methyl-pyrrolidin-2-yl)-phosphonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester ethyl ester 在 sodium tungstate 、 双氧水 作用下， 以 乙醇 、 水 、 正戊烷 为溶剂， 反应 73.0h， 以45%的产率得到(2-Methyl-1-oxy-3,4-dihydro-2H-pyrrol-2-yl)-phosphonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester ethyl ester
  参考文献：
  名称：

  Synthesis and Spin-Trapping Behavior of 5-ChEPMPO, a Cholesteryl Ester Analogue of the Spin Trap DEPMPO

  摘要：

  5-(Cholesteryloxyethoxyphosphoryl)-5-methylpyrroline N-oxide (5-ChEPMPO), a DEPMPO analogue bearing a cholesterol group on the phosphorus atom, has been prepared and used to trap peroxyl-, alkoxyl-, thiyl-, and carbon-centered radicals in organic solvent. The important steric hindrance in 5-ChEPMPO does not affect the properties of 5-ChEPMPO in comparison to DEPMPO for the spin trapping of an enantiopure linoleic acid hydroperoxide. The 5-ChEPMPO-OOL spin adduct was observed by ESR and confirmed by ESI-MS/MS experiments. The relaxation terms of the 5-ChEPMPO-lipid peroxyl spin adduct were compared with those of other peroxyl spin adducts, and it was shown that the cholesteryl group has only a weak influence on the exchange rate between adduct conformers.

  DOI：

  10.1021/jo0517390
• 作为产物：
  描述：

  、 2-甲基吡咯啉 在 三氟化硼乙醚 作用下， 反应 120.0h， 以66%的产率得到(2-Methyl-pyrrolidin-2-yl)-phosphonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester ethyl ester
  参考文献：
  名称：

  Synthesis and Spin-Trapping Behavior of 5-ChEPMPO, a Cholesteryl Ester Analogue of the Spin Trap DEPMPO

  摘要：

  5-(Cholesteryloxyethoxyphosphoryl)-5-methylpyrroline N-oxide (5-ChEPMPO), a DEPMPO analogue bearing a cholesterol group on the phosphorus atom, has been prepared and used to trap peroxyl-, alkoxyl-, thiyl-, and carbon-centered radicals in organic solvent. The important steric hindrance in 5-ChEPMPO does not affect the properties of 5-ChEPMPO in comparison to DEPMPO for the spin trapping of an enantiopure linoleic acid hydroperoxide. The 5-ChEPMPO-OOL spin adduct was observed by ESR and confirmed by ESI-MS/MS experiments. The relaxation terms of the 5-ChEPMPO-lipid peroxyl spin adduct were compared with those of other peroxyl spin adducts, and it was shown that the cholesteryl group has only a weak influence on the exchange rate between adduct conformers.

  DOI：

  10.1021/jo0517390